With painter Roy Kiyooka and architect Clifford Wiens, this group shared a common professional commitment and became a small but active artistic community in Regina. Having studied in central Canada, the United States, and Europe, before moving to Regina, the Regina Five combined the major currents of abstract expressionism in the context of 1950s Saskatchewan.

In 1958, Ronald Bloore, then the director of the Norman Mackenzie Art Gallery, brought national and international exhibitions to Regina. These exhibitions underscored the originality of the Regina Five's work. The Regina Five's bold, nonfigurative paintings represented a new direction in abstract painting in Canada and reflected influx of advanced ideas arriving through the channel of the annual Emma Lake Artists' Workshops.

The painters came to national attention in 1961, when Bloore organized "The May Show" to coincide with the meeting of the Canadian Museums Association, an exhibition which featured the five painters plus sculptures by Wolfram Niessen and architectural drawings and models by Clifford Wiens. The exhibition inspired Richard B. Simmons, Coordinator of Extension Services at the National Gallery of Canada, to select work of the five painters for a travelling exhibition that appeared later that year in Ottawa.